13984-53-7

Usage

Uses

Used in Chemical Synthesis:
METHYL 4-ACETYL-5-OXOHEXANOATE is used as a synthetic intermediate for the preparation of various complex organic molecules. Its β-ketoester structure allows it to participate in a range of reactions, such as condensation and Michael addition reactions, which are crucial for the synthesis of target compounds.
Used in Modified Knorr Condensation:
In the field of heterocyclic chemistry, METHYL 4-ACETYL-5-OXOHEXANOATE is used as a reactant in modified Knorr condensation, a widely employed method for the synthesis of pyrroles. This reaction allows for the formation of diverse pyrrole derivatives, which are important in pharmaceuticals, agrochemicals, and materials science.
Used in the Synthesis of Dibenzyl-3,6-Dimethylpyrazine-2,5-Dicarboxylate:
METHYL 4-ACETYL-5-OXOHEXANOATE is also utilized in the preparation of dibenzyl-3,6-dimethylpyrazine-2,5-dicarboxylate, a compound with potential applications in the fragrance and flavor industry. Its unique structure contributes to the formation of the desired product, showcasing its versatility in organic synthesis.
Used in Analytical Chemistry:
METHYL 4-ACETYL-5-OXOHEXANOATE can be employed as a reference compound in analytical chemistry, particularly in gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) techniques. Its distinct chemical properties and fragmentation patterns make it useful for identifying and characterizing the Michael addition product in various reaction systems.

InChI:InChI=1/C9H14O4/c1-6(10)8(7(2)11)4-5-9(12)13-3/h10H,4-5H2,1-3H3/b8-6+

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 123-54-6 acetylacetone 
• 15435-71-9 sodium acetoacetonate 
• 6001-87-2 methyl 3-chloropropionate 
• 3395-91-3 Methyl 3-bromopropionate 
• 26577-95-7 bis-(3-methoxycarbonyl-propionyl)-peroxide 

Downstream Products

• 2386-37-0 ethyl 3,5-dimethyl-4-(2-methoxycarbonyl-ethyl)pyrrole-2-carboxylate 
• 115997-51-8 benzyl 4-<2-(methoxycarbonyl)ethyl>-3,5-dimethyl-((15)N)pyrrole-2-carboxylate 
• 2510-27-2 2-(3,5-dimethylisoxazol-4-yl)acetic acid 
• 890625-93-1 3-(3,5-dimethyl-1H-pyrazol-4-yl)propanoic acid 
• 956352-96-8 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoic acid 
• 504-02-9 1,3-cylohexanedione 
• 20303-31-5 benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 102441-95-2 dibenzyl 3,6-dimethylpyrazine-2,5-dicarboxylate 
• 31837-62-4 benzyl 4-<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate 
• 358721-54-7 3-(3,5-dimethyl-4-isoxazolyl)propanoyl chloride 
• 116423-07-5 β-(3,5-Dimethyl-4-isoxazolyl)propionic acid 
• 6792-12-7 19-oxovincadifformine 
• 60024-89-7 4-(2-methoxycarbonylethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 16132-20-0 tert-butyl 3,5-dimethyl-4-(2-methoxycarbonylethyl)-1H-pyrrole-2-carboxylate 

Relevant academic research and scientific papers

Preparation method of delta-caprolactone

The invention relates to a preparation method of delta-caprolactone. The method comprises the following steps: dissolving a beta-dicarbonyl compound and a basic catalyst in a solvent, and conducting preheating; dropwise adding alkyl acrylate into a reaction system for a Michael addition reaction; cooling the system, adding alkali, and then heating the reaction system for saponification reaction; adding water, cooling the system, and adding a reducing agent for reaction; and cooling the system, adjusting the pH value with acid, and carrying out post-treatment to obtain the delta-caprolactone. The method disclosed by the invention is simple in process operation, high in safety, high in raw material utilization rate, short in total consumed time and free of generation of carbon dioxide.

Method for preparing 1, 3-cyclohexanedione

The invention discloses a method for preparing 1, 3-cyclohexanedione. The method comprises the following steps: 1) dissolving acetylacetone and a catalyst in a solvent, adding acrylate into a constant-pressure dropping funnel, and dropwise adding acrylate into a reaction system, after drop-by-drop adding, heating to 60-80 DEG C, and continuously reacting for 0.5-1 hour; and 2) after the reaction is finished, cooling to 40 DEG C, adding a solid condensing agent, heating the reaction liquid to 40-50 DEG C, continuously reacting for 1-1.5 hours, concentrating under reduced pressure to remove the solvent and methyl acetate and other low-boiling-point byproducts generated by the reaction, then adding a small amount of water, adjusting the pH value to 1-2 by using hydrochloric acid (1.1-1.2 equivalent), cooling to separate out a product, centrifuging, leaching by using a small amount of ice water, carrying out pulping treatment by using ethyl acetate, filtering and drying to obtain the 1, 3-cyclohexanedione product.

Design and synthesis of high affinity inhibitors of Plasmodium falciparum and Plasmodium vivax N-myristoyltransferases directed by ligand efficiency dependent lipophilicity (LELP)

N-Myristoyltransferase (NMT) is an essential eukaryotic enzyme and an attractive drug target in parasitic infections such as malaria. We have previously reported that 2-(3-(piperidin-4-yloxy)benzo[b]thiophen-2-yl)-5-((1,3, 5-trimethyl-1H-pyrazol-4-yl)meth

Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations

Carbon dioxide can be used as a temporary protecting group for amines. A carbamic acid is formed reversibly when CO2 is bubbled through a solution of a sufficiently basic primary amine at room temperature and atmospheric pressure. This reaction is employed for the protection of the amine functionality in several reactions at room temperature where inter- or intramolecular selectivity is desired. The concept is demonstrated for the selective Michael additions to methyl acrylate of a normally less reactive sulfonamide in the presence of a strong amine nucleophile, or of a cyclic secondary amine in the presence of an aliphatic primary amine, or of a β-ketoester in the presence of amines. The selective acylation of an alcohol in the presence of an amine can be achieved under a CO2 atmosphere as well.

Poly(N-vinylimidazole) as efficient recyclable catalyst for the Michael addition of CH-acids to electron deficient alkenes in water

Efficiency of poly(N-vinylimidazole) as the basic recyclable catalyst for the Michael addition of CH-acids to acrylonitrile, methyl acrylate, methyl vinyl ketone and methyl vinyl sulfone in water at ambient temperature was studied. In these reactions, formation of both 1 : 1 and 1 : 2 adducts is possible.

Synthetic porphyrins bearing β-propionate chains as photosensitizers for photodynamic therapy

Porphyrins with different numbers of β-propionate chains mimicking natural porphyrins were prepared via the 2+2 MacDonald type approach. Photodynamic activity against WiDr colon adenocarcinoma cells showed that activity is related to the number of β-propi

Process For Preparing Porphyrin Derivatives, Such As Protoporphyrin (IX) And Synthesis Intermediates

The present invention relates to a process for preparing a porphyrin of formula (I), optionally in the form of a salt with an alkali metal and/or in the form of a metal complex: in which: R and R′ are as defined in claim 1, comprising: a step of condensation, in an acidic medium, between a dipyrromethane of formula (II): in which R′b is as defined above for (I), and a dipyrromethane of formula (III): in which R″ is as defined in claim 1, and also the compounds of formula (III).

Fast carbon-carbon bond formation by a promiscuous lipase

Lipase B from Candida antarctica was redesigned to catalyze the promiscuous reaction of carbon-carbon bond formation. Mutation of the catalytic serine to alanine afforded a mutant that catalyzed Michael additions of 1,3-dicarbonyls to α,β-unsaturated carbonyl compounds at high specific rates, such as 4000 s-1. The enzyme-catalyzed Michael addition reaction followed saturation kinetics and showed substrate inhibition. The designed enzyme showed high rate enhancements with a catalytic proficiency higher than 108, which is on the same level as that observed for enzymes with native substrates. Copyright

Synthesis of a new lipophilic bilirubin. Conformation, transhepatic transport and glucuronidation

Analogs of symmetrical bilirubin isomers with vinyl groups replaced by n-butyls (1 and 2) were synthesized and found to be much more soluble in nonpolar solvents than either bilirubin itself or its analogs with ethyls in place of vinyls (3 and 4). The increased lipophilicity of 1 and 2 allowed, for the first time, vapor pressure osmometric molecular wt. determinations of a bilirubin acid, showing in CHCl3 solvent: MW(obs)=632±10 for 1, and 637±10 for 2 (both formula weight 644) - data that clearly indicate monomers and no dimers. The induced circular dichroism (ICD) spectra of 1 and 2, with negative exciton chirality Cotton effects, are quite like those of 3 and 4 in chloroform containing quinine, but the ICDs in aqueous buffer containing human serum albumin differ considerably. Rubins 1, 3 and 4 exhibit dissimilar but positive exciton chirality Cotton effects, while 2 shows a negative exciton chirality Cotton effect. The metabolism of the n-butyl rubins in the rat is highly dependent on the specific endo or exo location of the n-butyl groups. Rubin 2, with two endo n-butyl groups was metabolized rather like the corresponding mesobilirubin (4) or natural bilirubin itself, being converted to a mono and diglucuronide that were excreted promptly in bile. The presence of the bulky endo-n-butyl groups and the high lipophilicity of the compound seemed to interfere with glucuronidation in the liver only slightly. In contrast, the similar, yet even more lipophilic n-butyl rubin 1, which has two exo n-butyl groups, was glucuronidated and excreted in bile in the rat rather poorly. (C) 2000 Elsevier Science Ltd.

Synthesis of Vinca Alkaloids and Related Compounds. 90.1 New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine

The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (±)-3-oxominovincine (14). Regioselective reduction of 14 furnished (±)-minovincine (17).